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8 minute read · Published September 16, 2024

How to win with your startup by leaning into your own weirdness

Latest Update September 16, 2024

We're told startups are simple: break things down into neat phases, follow the playbook. Have an idea, test it, learn, grow. Rinse and repeat. This usually happens when we listen to other founders' stories.

"Oh, they validated their idea this way, so should we."

"They pivoted like that, so that must be the right approach."

We end up knee-deep in "analysis,", hypnotizing ourselves there's a HUGE market ripe for disruption, RIGHT now. We tell ourselves our startup will definitely be a $1B outcome? Every data point starts to predict success.

Then you launch.

The playbook falls apart. The plan you copied from a billionaire goes wrong. Prospective users stop responding. And the few responses you do have contract your gut feeling. The data points left, but your instincts scream right.

As a founder, you'll rarely have perfect, conclusive information. How do you make confident decisions anyway? How do you know when to listen to your intuition vs. when to copy what worked for others?

The importance of your founder “sound”

Watch this video of guitarist B.B. King at 07:41 about his approach to phrasing:    

"I try to make it more personal, I try to put more ME in it. I think of my playing like we do Doctors. Some are MDs, others are specialists. So I thought I'd specialize in the Blues in the way I play them."  

B.B. King was a legendary blues guitarist who was pretty average at playing the guitar.

He didn't become a legend because of his technical mastery. B.B. found his "sound" - his unique style - and played the shit out of it. His genius was in soulful phrasing, heart-wrenching vibrato, and these insane bends that just…ugh. He specialized in being unmistakably "B.B. King." Confidence in his intuition. Tunes played only in the way he hears them. This is what differentiated him and cemented his legacy as a musician.

It's not just B.B. For my hip-hop heads, think about J. Cole – poetic, beautifully lyrical, and introspective. Or Mac Miller (RIP), who came in with a sound many thought corny, but developed an incredible flow and depth. In the pop world, there's Ed Sheeran - not the most powerful voice, but his songwriting and sincerity connect with millions (not me though.)

They all found their sound. Trusted their gut feeling and leaned into their own uniqueness.

This extends beyond music. Founders, too, ought to inject more of themselves into their companies. Artists found success by leaning into their unique strengths and perspectives. Startups aren't so different. As cliché as it is, you really cannot sacrifice your identity for short-term success.

Can’t code? That’s ok! You've seen the founder who raised $100M off a napkin sketch and 3 bullet points. That could be you, dude. Your lack of technical background might be your superpower - maybe you understand the problem better than any engineer ever could.

Okay, and for the technical counterparts. There's magic in seeing an idea come to life. Maybe you're not a visionary fundraiser but let your product do the talking. Build something so good investors can't ignore it. Your product becomes your pitch.

Use what's natural to you as your weapon – bring your whole identity to the table. Your personality, your quirks, your way of seeing the world. That's your edge. Just like the best musicians, the best founders find their "sound". Steve Jobs wasn't the greatest engineer, but he leaned into his great taste and his persuasion skills.

Building companies is just as much art as making music is. In this article, you'll discover how to find your founder sound.

Don’t be a copycat

It's tempting to follow what worked for others. Your buddy raised from Sequoia with a bare-bones MVP, so you should copy that, right? Or maybe it's time to build a "compound startup" because it worked for Parker Conrad, and you're... kind of like him (if you squint really hard)?

Not so fast. This kind of pattern matching can be a recipe for disaster. It's like B.B. King trying to be the best technical guitar player.

Take fundraising. Picture this: You've cobbled together a pitch deck from "successful" examples. Slides from Company X, go-to-market from Company Y, projections mirroring Company Z. You make it through the pitch in front of the famous VC.

You leave the pitch feeling good, but the response doesn't have a termsheet.pdf attached: "Thanks, but I just couldn't get excited about the business."

Sometimes that's just fundraising. But the best investors are looking for your edge. Who are you and what’s your story? What are you seeing that everyone else missed? It's called a unique insight for a reason, not an aggregated insight.

We fall into this trap because we're drowning in case studies and "proven" strategies. If you tried to follow them all, you'd end up doing nothing. This is where your founder sound becomes crucial. You need to recognize your style and decision-making process. Just as B.B. King "heard" the blues his way, you "hear" your business in a particular way.

So, what's your sound? Let's explore some common ones I've observed...

Different types of founder "sounds”

Just like musicians, founders are wired to approach their craft differently. Some founders dive head-first into building, others obsess over market research, and some won't sleep until they've talked to a hundred potential users.

I've talked to a ton of founders, and so far I’ve come across:

1. The Futurists (EDM)

You're all about data and trends. You see the future, and your ideas often have a moonshot vibe. You're planning for tomorrow before others even realize what's happening today.

Think: Patrick Collison at Stripe. He saw a future where internet payments could be seamless when most were still struggling with clunky systems.

2. The Pragmatists (Indie)

That's me. We live for practical solutions and incremental improvements. Usually we rely more on user interviews and conversations. We look at existing processes and think, "How can we make this more efficient?" Simple reads on the market, straightforward products.

Think: Jason Fried at Basecamp. Focused on solving real problems for real people, without the Silicon Valley hype.

3. The Analysts (Classical)

You're not happy unless you've modeled every situation. In a past life you might have been a finance bro/sista. You approach your startup methodically, ensuring every decision is backed by solid data and reasoning. Spreadsheets are your love language.

Think: Benoit Dagevill at Snowflake. Who'd have thought we needed another data warehousing solution? He did…and he was totally right.

4. The Storytellers (Ballads)

You need strong proof points and real traction. You're all about selling the vision and building a narrative. Your startup is a compelling story, and you won't launch until you're sure it resonates with your audience.

Think: Brian Chesky at Airbnb. He turned the idea of staying in strangers' homes into a compelling narrative about…belonging anywhere. How does he see the world so differently?

Don't worry if you don't neatly fit into these categories. Hopefully there are some elements that resonate with you. And if not, let's go through some ways to figure this out…

How to actually find it

At this point, I hope your mind is active and you're doing some internal digging. But if you're new to developing this skill (your sound), I'll teach you. Stay with me; it might get a little weird.

Look at the shirt you're wearing. Why did you choose it? For me, I'm wearing a Represent shirt with a shark on it. It cost $80 and it's pretty basic. But it feels high quality and has a bit of edge (or so I think!).

This extends to the products I build. They're a little basic (my first company is a B2B construction software), but refined. Simple components, clean design, nothing too flashy, but we did use yellow as a brand color. 

This philosophy further extends to my feature selection and validation process. I shy away from moonshots, prefer straightforward market "reads" and uncomplicated products. I’m not going to radically launch a feature, I prefer to slowly test my way there. This feels natural to me. I might slowly add a bit more pieces as I grow.

Your style might manifest differently. Maybe your shirt has a bold pattern. Or something vintage. Or you love wearing the same White Tee every day. The free Huel shirt (guilty)?

Your personal preferences reveal a lot about your business decisions, your sound. It's not a 1:1 match, but a starting point for developing your product sense.

It also works in reverse: What's something you'd never wear? That says just as much. I'd never wear a scarf. It feels superfluous and ostentatious. I'd rather blend in. Operate in the shadows.

This translates to business: my mind shies away from big product launches and splashy events. The less attention, the better.

Leveraging your sound in business decisions

Now that you've started to identify your founder sound, let's explore how it influences how you build.

Say you've decided to tackle a problem in the restaurant industry. You love food and food loves you. How might different founder sounds approach this?

The Pragmatist (Indie) approach:

In your user interviews with restaurant owners – you might uncover that restaurant owners see a drop off in "We get plenty of foot traffic, but our takeout orders are almost non-existent during lunchtime." You dig a little deeper and…

Your unique insight: There's a gap in awareness about takeout options from local eateries during peak lunch hours.

So you think, "Let's keep this simple." You develop a straightforward app that aggregates takeout menus from nearby restaurants and targets local offices with quick, easy ordering options. No bells and whistles—just a practical solution that connects busy workers with local lunch spots they didn't know existed.

The Futurist (EDM) approach:

You might envision a future where inventory management is completely hands-off. So you think, "What if restaurants didn't have to think about inventory at all?" And so, you’re off to the races – an LLM that tracks inventory based on sensors! It’s an AI employee that….

The Analyst (Classical) approach:

You might dive deep into the data behind restaurant operations. So you think, "How can we optimize every aspect of the supply chain?” You might streamline…renegotiate prices with every…the cups…the etc…figure out ways to optimize staffing!

The Storyteller (Ballads) approach:

You might focus on the human connections within the restaurant industry. So you think, "How can we empower local eateries and connect them with their communities?" So….you create Tiktok…

Developing conviction – why is it so hard?

We're afraid of making mistakes. We’re afraid of not being good enough. Maybe still haunted by that time your mom yelled at you for spilling milk. Or a micromanaging boss made us second-guess everything. Whatever it is, you're holding onto results too tightly – and it’s rooted in fear.

When musicians try too hard to "sound good," to "play correctly", they lose the natural tempo, the swagger they have when they're just jamming or singing to themselves. But, why is it that when we practice alone is when we sound the best?  

The Piano practice book that helps you tine into your founder sound

Effortless Mastery by Kenny Werner contains one of the most profound things about this. It’s a piano practice book. Werner prescribes an exercise where you drop your hands on the piano and tell yourself, "That is the most beautiful sound I have ever heard." It could be the most dissonant, ear-wrenching sound, but still "the most beautiful."

You repeat this over and over to train yourself to not judge your playing. This exercise forced me to separate the act of creation from judgment. In startup terms, it's like truly believing every iteration is a win, even if it fails. It's all part of the process.

Can you imagine approaching your business with that level of confidence? Navigating the uncertainty with fearlessness, trusting you'll adapt to any mistake? Personally I hope I can get there someday.

When does intuition just become bias?

Don't mistake your founder sound for permission to overrule what customers think and go with your first assumption. It's important to understand when bias leads you astray. 

Trusting yourself and having confidence doesn’t mean ignoring feedback. There is a delicate balance between pushing forward and adjusting your approach. It’s a skill that will take time to develop and should evolve as your startup evolves. Be willing to adapt when the evidence suggests it’s time for a change.

This journey is deeply personal. You're dedicating years of your life and 10,000+ hours to this. Entrepreneurship is YOUR form of self-expression, your art. It's how you carve out your space in the world. Trust yourself. 

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